The life of the Winchesters
by JaydenWinchester
Summary: Sequel to Not an Evans a Winchester. These are just random one shots/ drabbles that show many moments during Gwens childhood.
1. Chapter 1: the car ride

The life of a Winchester

Part 2 in "The Real Family Business" verse.

 **Hey people this is my second story in my new series "The Real Family Business. The first goes by Not an Evans a Winchester. You don't absolutly need to read it to understand but I think it is worth the read. So the age difference between between the three are:**

 **Dean is 8 years older than Gwen**

 **Sam is 4 years older than Gwen.**

 **Also, once shots. There might be a few that have sequels to them but in general these are just one shots/** **drabbles.**

 **So** , **enjoy also please review.**

 **Dean: 11**

 **Sam: 7**

 **Gwen: 3**

* * *

It started in the back seat of the impala. John was driving fastly to another town and the three children were in the back seat. Dean was by one door looking out the window watching the town slowly disappearing, Sam was by the other door and was keeping watch on the small girl in the middle of them, Gwen was fast asleep in her carseat. Music was blaring from the speakers while the drive continued other than this the car was in complete silence.

"So, boys I know we were only there for a few weeks but…" John started but Dean cut him off.

"We know dad, another town needs our help." Dean said quietly. John had taken the boys out of school early today because the next hunt had been far away and they were needed soon. Sam had been pouty when he was informed that they weren't coming back but Dean hadn't minded that much.

"Sam, look."John started but Sam cut him off with a small smile.

"It's okay dad." Sam said. Gwen then started to wake up and smiled when she saw they were in the Impala.

"Da?" She called. John grinned and looked back at the small girl with jet black hair and big green eyes.

"Yes Gwen?" He asked. She giggled and looked over at Dean, she then reached over and pulled on his shirt.

"De?" She asked, her eyes were filled with worry. She felt the sadness in the car and she wanted to know what was wrong. Dean smiled and patted her arm.

"I'm okay Gwen." Dean whispered. She scrunched up her face and tried one more more time.

" 'ammy?" She asked. Sam gave her a sad smile.

"We are just moving again it's okay Gwenny." He said. Gwen nodded before she turned to the other side and placed her hand on Deans arm again.

"Gunna be otay De." She said. Dean smiled at her and she smiled back. The rest of the car ride was silent. Though this time it was a more comfortable silence.


	2. Chapter 2: Thumb sucking

The life as a Winchester.

Thumb sucking

Dean: 8

Sam: 4

Gwen: 17 months.

Gwen slightly changed when Lilly passed away, but a few things didn't change. She still carried her stuffed 'padfoot' around by its ear. She still prefered her juice than water or milk. She also still sucked her thumb. More times than not Gwen would be found sitting or lying next to Sam and Dean holding her padfoot with her left hand and her right thumb in her mouth, sucking away. Now Sam and Dean didn't mind this habit at all, they actually found this kind of cute. John on the other hand didn't like this. He tried to get her out of this habit but when ever he tried all she did was look up at him wide eyed, and gave him a betrayed look. So he left it alone for a while but that didn't last that long.

"Come on daddy, it isn't hurting anyone." Sam said. John didn't listen and got on the ground, padfoot in hand. Gwen looked at the toy with interest and John smiled.

"Gwen, if you take your thumb out of your mouth I will give padfoot back." He said. Gwen looked at the toy and back to her thumb. Sam watched the scene with interest, he wanted to see what his cousin was going to pick. To Johns shock Gwen stuck her thumb right back into her mouth and crawled away from him.

"Give it a rest Dad, Gwen will take it out when she finds something to do or play with. She always does." Dean said as he walked into the room with Gwen in his arms, who was now asleep. John sighed and nodded, it wasn't hurting anyone at the moment.

Dean: 18

Sam: 14

Gwen: 10

Gwen was sitting in the back seat while Sam was sitting in the front next to Dean who was currently driving them to a random town that their dad was meeting them at. Sam had fell asleep a while back and Dean was singing along to a song that had been on the tape that Gwen and Sam made for him as a sweet sixteen present. Dean swore that this tape was his all time favorite and he would never lose it. They knew this was true, sadly Gwen regretted making it because he had it on repeat when he drove them to towns. Gwen was now in the back, fast asleep, and her thumb was in her mouth. Dean watched her from the mirror and he sighed. She had never stopped this habit, but like back then he and Sam thinks it is cute. So they never told John about the small habit. Gwen pulled her ratted dog close to her in her sleep and cuddled close to herself and sighed happily. Dean knew she was in a deep sleep so she wasn't going to wake up at the next stop, he also knew that Sam would climb in the back at the next stop and they would cuddle up together, because that was what always happened. This is how they did it when they were all kids and that was how they would do it when they were all old and about two drop.


	3. Chapter 3: being their big brother

The life as a Winchester.

Being their big brother

Dean:13

Sam:9

Gwen:5

okay I know this one was really short but I think it's cute.

* * *

Dean sometimes hated being a big brother. It was hard keeping a watch over the younger two at times and a good portion of the time they drove him crazy. Sam would argue with their dad all the time and Gwen was always following him around the motel and could hardly stay quiet for longer than five minutes. Sometimes he would rather be with a friend or sucking faces with a girl at school. Sometimes he missed out on a date or to because of Sam and Gwen and he would rather be on that date with the current girl he was hooking up with. Don't get him wrong he didn't blame them for it but he did want to go on that date. He really wished that dad didn't force him to watch them.

"De, will you wead to me?" Gwen asked climbing onto his bed. Sam looked over and saw Gwen handing Dean 'The Lion, Witch, and The Wardrobe' to Dean and he smiled.

"Get over here Sammy." Dean said. Sam smiled and climbed onto the bed. Dean smiled and started reading the book to them and Gwen quickly fell asleep.

Who was he kidding he loved being a big brother, after all they were his to take care of


	4. Chapter 4: valentines day

The life as a Winchester.

Valintines day

Dean:17

Sam:12

Gwen:8

oh and as for the last chapter, I know Dean was only thirteen. I also said he would rather be doing it. Not that he was. He is a teenager after all.

* * *

Gwen knew she probably shouldn't have said anything, after all Sam and Dean were protective of her. She just couldn't help it though, she was so excited when he did it and she couldn't not have said anything. Though she should have saw it coming, she really should have. Let's back up it started on Valentine's Day at school.

~7:30 that morning~

Gwen smiled brightly at Sam who was the one who walked her to school that morning, Dean had to leave early that day because their dad needed something from the Library and Dean was all for skipping school.

"Have a good day munchkin." Sam said.

"Bye Sammy." Gwen said as she walked into the school building. She then ran to her classroom and saw that her classroom was filled with hearts and that each kids desk had construction papers on it. They also had small boxes on their desk. She recognized the boxes as the ones they had made decorated that week. She walked over to her desk and waited for the teacher to tell them what they were doing that day. A few minutes passed and the teacher walked to the front of the classroom and smiled at them.

"Goodmorning class, today we are making Valentines day cards." She said. Gwen smiled and the teacher told them what they had to do and she then sent them off. Gwen first made a few cards for her family; John, Sam, Dean, Celeb, Pastor Jim, and Uncle Bobby. She then started on the cards for her friends in the class. She soon finished her cards and put the ones for her friends in their boxes. When the teacher told them that time was up and they could look at their cards she saw she had one from each of her friends, we'll all but her friend Allan. She frowned and looked at her friend who gave her a shy smile. She then read her cards and smiled, feeling a little better. The teacher then told them to put the cards back into the box and she then handed out cookies and put a movie on, they normally wouldn't have done this but it was a Friday so it worked out for them. After the movie was over the teacher told them it was their lunch break so she had them line up. She stood behind Allan and she frowned again, she didn't know what she did to make Allan not give her a card. This was confusing her allot. Once they got to the lunch area they all scattered so they could eat with their friends. Gwen chatted with her friends, but Allan stayed quiet when they ate. They were soon released to the play area and Allan finally walked up to Gwen.

"Hey Gwen." He said quietly.

"Hi." Gwen replied.

"Um, can you walk with me?" He asked. Gwen nodded and Allan started heading over to the slide. Gwen was confused when he pulled her under the slide. Her confusion was soon gone when Allan gave her a card.

"Gwen, I like you allot." He said. She then read the car which said

'I really like you, be my girlfriend?' She then smiled at him and blushed.

"Yeah, I mean um... I would love to be your girlfriend." She said. He then leaned in and kissed her cheek. The bell then rang, signaling that they needed to go back to class. Allan grabbed her hand and they walked to the class room. The teacher had put another movie on when the class was back inside and Gwen sat next to Allan this time. When school got out Allan and Gwen walked out hand in hand and Gwen smiled warmly at him. When Allan saw his mom he quickly kissed her cheek again and ran off. Gwen then sat on the bench outside and waited for Sam or Dean to walk over. She didn't have to wait long though because Sam soon walked over to her.

"Hey munchkin how was school?" He asked.

"It was fun, the teacher let us make cards and we ate cookies with frosting and sprinkles on them. She also put on a movie for us." Gwen said. Sam smiled and Gwen handed him his card.

"Thanks Gwen." He said. She smiled and he grabbed her hand so they could walk back to the motel. The walk was quiet but that was normal for them. Gwen was still excited about her new boyfriend and wanted to tell everyone, but she didn't want to explains this to both Sam and Dean at different times so she stayed quiet. Once they got back to the motel she saw Dean in the kitchen and she ran up and hugged him.

"Hey squirt, how was your day?" He asked.

"It was fun, but I have to tell you and Sammy something." She said. Sam gave her a confused look and Dean gave her an amused one.

"Okay, so tell us." Dean said.

"I got a boyfriend!" She said excitedly. This time Sam had an amused look on his face but Dean glared.

"No boyfriends." He said. Gwen gave him a confused look.

"But Dean, Allan said he liked me and I like him so we have to go out." She said, obviously not understanding the concept of dating.

"No boyfriends, you are eight years old." Dean said. Sam then decided to step in and save their cousin who was more like a sister.

"How did Allan ask you to be his girlfriend?" He asked. Gwen handed Sam the card Llan gave her,

"He gave me this under the slide." Gwen said. Sam almost laughed but Dean paled.

"Under the slide huh, what else he do?" Dean asked.

"He kissed my cheek." Gwen said. Dean glared and Sam paled slightly.

"Um Gwen, I agree with Dean on this one." Sam said, Gwen was about to complain but Sam cut her off.

"Dad found another job and we are leaving this weekend anyways." Sam added. Gwen nodde in understandment and walked to her room, but not before giving Dean the card she made him. Dean smiled, knowing the sine she forgives him.

"Well that was a close call." Dean said. Sam snorted a bit and shook his head.

"She is eight, she doesn't understand this stuff. Plus if anything I bet she would stop being his 'girlfriend' in a week even if we did stay." Sam said. Dean gave him a confused look and Sam smirked.

"It's Allan, you know the boy who was her best friends 'boyfriend' a week ago." Sam said. Dean then paled before glaring.

"Son of a bitch." He said.

* * *

By the way this was actually based on something that had happened when I was in third grade. Well minus the it being Valintines day and over protective brothers. My friend, who had been a friend of mines 'boyfriend' had asked me out at recess under a slide. He wrote down 'I love you' on a paper and handed it to me. Me being my third grade self had thought this was the best thing in the world and well long story short we broke up after the school year ended. Though it wasn't an official break up it was just we weren't boyfriend-girlfriend anymore.


	5. Chapter 5: Halloween

**The life as a Winchester.**

 **Halloween and bullies**

 **Dean: 17**

 **Sam: 13**

 **Gwen: 9 1/2**

 **sorry if this one is short.**

* * *

Dean was worried, Gwen had been a little pale when he had picked her up from school and she hadn't spoken a word since. At first Dean had assumed that she had been a little sick but she wasn't warm and she had shook her head when he asked if she was feeling sick. Though he knew he had to snap her out of this before dad came home. He wouldn't be that happy.

"Gwen, i need to pick up Sammy. You want to come?" He asked. She shook her head and she crawled onto the motel bed and climbed under the covers.

"Hey, thought you wanted to see Sammy." Dean said. That morning Gwen was going on and on about how she wanted to see the middle school campus and how she couldn't wait to be a big kid so she could be on it all the time. Though something changed her mind between seven that morning and now.

"Come on. I will let you stay in the car." Dean said. She nodded and let Dean pull her out of the tub. They then started to head to the car and Gwen laid down in the back and she curled up as he started the car. They soon pulled up to the school and before Gwen knew it Sam was sitting in the front seat and they were leaving.

"So Sammy, how was your day?" Dean asked.

"It was cool. We played soccer in P.E. today and I passed my science test." Sam said.

"Thats cool Sam." Dean said. Sam then looked in the back seat and saw Gwen laying there.

"Whats up with Gwen?" Sam asked.

"No idea, she was quiet all afternoon and she seemed a little pale when i picked her up." Dean said. Sam nodded and looked at her again. When Dean stopped at a stop sign Sam climbed into the back and pulled Gwen onto his lap. Gwen cuddled close to him and Sam started petting her hair. Gwen sighed but she didn't say anything. She just closed her eyes and drifted off.

"She seems tired." Sam said.

"Yeah, she almost fell asleep when we got back to the motel." Dean said. Sam didn't reply to this and he continued petting Gwen's raven locks as they drove back to the motel. Before the boys knew it they were back and Sam was carrying Gwen back to the room. Luckily Gwen has yet to hit her growth spurt so she was still small. Once they got back to the room Sam put Gwen to bed and Dean looked through her backpack. It didn't have much, just her homework that had been completed the night before and a few other things like books and school supplies. Sam shook his head as Dean looked through her bag and turned on the T.V. Sam then flipped through some channels and he passes the movie 'Hocus Pocus' as he did.

Dean sat down near Sam and sighed, he had no idea what could have set this off.

"She will tell us when she is ready. It's not like she takes to long to tell us." Sam said.

"True, but i am worried about her." Dean said.

"Same here." Sam said. Sam then pulled out his homework and Dean watched some random movies that was playing. Before they knew it Gwen woke up from her nap and Dean was taking a quick shower. When Sam saw that she was up he motioned over.

"Come on, let's watch a movie." Sam whispered to Gwen. Gwen then got up and walked over to Sam and Sam turned on the t.v.

"Hey look Gwen, it's a Peanuts special." Sam said, trying to get her to smile. Though this did the opposite and Gwen's eyes filled with tears. Sam looked at her and Gwen got up and sat on Sam's lap.

"Did mommy hate me?" She whispered.

"No, why would you think that?" Sam asked.

"Brice said that my mom must have hated me if she died. He said that I didn't deserve a mom anyways because i am stupid." Gwen said sadly. Sam glared and shook his head.

"Your mom died to save you. Your mom loved you so much Gwen. Don't let some stupid kid tell you otherwise." Sam said softly. Gwen nodded and sniffled a little.

"Thank you Sammy." Gwen whispered. She then cuddled close to him and looked at the t.v. Neither of them noticed Dean exiting the bathroom or Dean shaking his head and chuckling to himself. They didn't even notice Dean snapping a picture of them curled up together on the couch, both of them had fallen asleep at this point anyways.

* * *

 **Well that was that. It took me a bit to come up with this idea. Well review.**


	6. Chapter 5 The next day

**The life as a Winchester.**

 **The next day**

 **Dean:17**

 **Sam:13**

 **Gwen:9**

* * *

To say John was shocked was an understatement, he was confused to say the least. That morning he got a call and he expected it to be from Deans school saying he needed to get his grades up or that Dean got into another fight. Nope it was from Sam's school, and well the fight part was right. So this is why he was sitting in the principals office with Sam and Gwen, why Gwen was there he has yet to find out.

"Mr. Winchester, as you know we are here because your son attacked Mr. Myers." The principal said. John nodded and Sam glared.

"He deserved it." Sam grumbled.

"Sam." John said in a firm voice and Sam looked down at his lap.

"Sorry sir." Sam mumbled. John nodded and Gwen looked at Sam in shock

"Sammy, you don't need to be sorry, you saved me." Gwen said. Sam chuckled and John gave Gwen a confused look.

"What does she meen by that?" John asked the principal. The principal looked at the man and nervously chucked.

"According to both of your children, um Mr. Myers had recently picked on your daughter." He said. Sam and Gwen both glared at the man and John looked at the two.

"Is that all?" John asked.

"Yes." The principal said as Sam and Gwen both said "No."

"Sam, Gwen what else happened?" John asked.

"Yesterday, Brice had told Gwen that Aunt Lilly hated her and that's why she died. He also said that Gwen was stupid and didn't deserve a mom. Today I saw Brice and his friend shoving Gwen around. Then Brice took Gwens backpack and dumped everything out of it. I started to run over there but before I could make it Brice pushed Gwen down the stairs. I um slid down the arm rail and caught her before she went down to many." Sam said sadly. Gwen nodded and John glared at the principal.

"You seemed to forget that little piece of information." John said. The principal stuttered a little and John shook his head.

"Are we done here?" He asked.

"Yes, um no I mean. Mr. Winchester Mr. Myers parents agreed not to sue but Samuel must be punished. We need to suspend him." The principle said.

"What's happening to Brice?" John asked.

"Um..." The principal started and John shook his head.

"Come on, let's get going." John then said. Gwen stood up and winced. She had twisted her ankle when she fell. Sam instantly bent down so Gwen could get on hai back but John stopped him.

"I got her Sam." John said. He then picked up Gwen and they left the building, the principal didn't seem to realize what had happened.

The car ride back to the apartment started silent but Sam broke that a few seconds in.

"Dad, I'm sorry." He said. John shook his head and patted Sam on the shoulder.

"No need, but what did you do to him?" John asked.

"When Sammy got me back up the stairs he pushed Brice down them." Gwen said. John shook his head again and smiled at his son.

"You did good Sam, you did good." John said.

* * *

 **Yeah I know, short. Couldn't think of anything and I wanted to write a sequel. So this was created.**


	7. Chapter 7: Blind

**The life as a Winchester.**

 **Blind**

 **Glasses**

 **Dean:13**

 **Sam:9**

 **Gwen:5**

* * *

At first they thought it was nothing, after all she always had that trouble. Though when John got called in to meet with her teacher they found out that this wasn't the case.

" , we have some concerns for your, daughter?" The teacher said, though to John it had sounded more like a question.

"Niece." John corrected. The teacher looked down at the file she had in front of her She then nervously chuckled before she looked back at John.

"Niece, right. Um, has Gwen always had a trouble with reading?" She asked. John glared slightly at her and the teacher took it as a no.

"Well, you see, Gwen has an issue reading the books we give them to practice reading. She can hardly read the things on the board." The teacher said. John nodded and the teacher continued.

"We have reasons to believe that Gwen will need to go to the eye doctor." The teacher finished.

"I will take her to get checked out." He said. James wore glasses so maybe it's hereditary. The teacher gave him a satisfied and she excused him.

John headed back to the apartment he was renting deep in thought. How would he pay for this? It wasn't like he had allot of jobs or insurance to do this. Maybe Bobby knew someone. John thought as he walked the cold streets. The second question on his mind was how come hasn't he been called in to a meeting before, she has been in school for a few months. John sighed as he opened the front door and walked into the small apartment. The first thing John saw was Dean heating up a bowl of spaghetti O's. The second was his youngest son working on flash cards with Gwen. Though he was standing a few feet away.

"Alright Gwen, now sound it out." Sam said patiently.

"Th-a-t. Th-a-t. That." Gwen said. Sam smiled at her and she clapped.

"Okay now try this one." Sam said as he flipped the cards. This time she squinted a little before she shook her head.

"Can't, too blurry." She said said miserably. Sam nodded as he put her cards away. John then walked into the kitchen with Dean.

"Hey dad." Dean said when he saw him. John smiled and ruffled his hair. Dean swatted his hand away before he served the bowls.

"Sorry there isn't much. Its all we had." Dean said.

"It's fine, we need to go shopping anyhow." John said. Dean smiled and he put the bowls on the small table.

"I'll call 'em in." John said. He then walked into the living room.

"Hey guys." John said. Gwen gave him a big grin and Sam laughed.

"Hey dad." Sam said.

"Hey Sammy, hey munchkin." John said. Gwen quickly got up and ran over to him, but she ended up bumping into his legs.

"Careful." John said. Gwen smiled as she walked to the table with help from Sam. Once they all sat down Dean cleared his throat.

"So, what did the teacher want?" Dean asked. John glanced at Dean and sighed.

"Gwen needs glasses." John said.

"I think we all knew that one." Sam mumered under his breath. Dean nodded in agreement and Gwen gave John a curious look.

"What glasses?" She asked. John then went on to explaine what glasses are. Sam and Dean gave each other a look as John talked to Gwen, this was going to be interesting.

~4 years later~

Contacts

Dean:17

Sam:13

Gwen:9

Gwen glared as Dean pulled her out of the car. She didn't like this at all, after the first time there she knew that this trip wouldn't be as plesant as she thought.

"Come on, you know the drill." Dean said. Gwen nodded as she got out of the car. She then let Dean drag her towards the familiar building.

"You know Dr. Vic, you liked him remember." Dean said. This calmed Gwen down slightly, he was her original eye doctor before Jihn found a hunter who did it, well he was the brother of a hunter. Though she still wasn't all that happy about this trip.

"Obviosly I don't." Gwen mumbled to herself. Dean gave her a look and she looked away. She hung out with Sam way to much, she was starting to sound like him.

"Oh well, if you want to help out on hunts..." Dean started. He has given this search a thousand times ever sense she found out about hunting.

"I know, I know. If I want to help on hunts then I should make sure nothing gets in the way." She said. Dean nodded as he began to pull her up the stairs to the office. Doctor Vic had a small eye place, though this was good because he helped out with vet hunters more than anyone else. Gwen was the first kid he worked with in years, which is why she always liked coming there instead of the other one.

"Welcome back Gwen." A cheerful voice called. Gwen nodded as she was guided to the backroom. She knew the preserver by heart at this point. First she gets her eyes scanned, then they get a reading on her persription. Then she would get sent back to Dean then she would be called in to read the letters and they would do the glasses thing. Though this time she assumed that she would also be doing something diffrent since they were back with Vic.

Pas predicted they went through the normal preserver though this time she was pulled to a table set up with a big bowl and a few more things. She then found herself having a woman putting contacts in her eyes.

"Alright now go back to your brother, we will call you back in a few minutes." She told her. Gwen nodded and she sat back with Dean.

"See, not so bad." Dean told her.

"You're right." She mumbled.

* * *

 **So I wrote two short stories and put them together to create this. Just to let you guys know this is set before the previous two chapters.**


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